I cast a vote for Oahu.. It is not Maui when it comes to kiting, but there are still plenty of days and Honolulu has certain ways of making it up to you ;]

Additionally if you get into foil / raceboards you can unlock a lot more "sea breeze" days at all places listed.

It goes without saying that LA is a fun town. The problem is if you want to party and live in the hills it can be a pain to get down to Long Beach to kite - places you have to drive to can sometimes take the fun out of things you're looking forward to doing in LA

Good luck on your adventures mate and save me a spot on the couch whereever you end up

nobody mentioned another important factor: cost of living. Unfortunately the Bay Area is catastrophic with that. Check the rent or housing prices first before you make a move. You have to understand that the Bay Area is much much more expensive than any of the other places that were mentioned here. I love the Bay Area, the wind is good (though there are plenty other places that are as good), for me its the combination of good tech jobs and the kitboarding that is unique. But you need to make good $$ in order to be ok here.

I have lived in OBX and Florida for kiting. I say hands down, SF Bay Area. Although cost of living is high - the other kite spots tend to have limited jobs. I have been living/working in Boston Area and can say the rent here is just as high as SF.

Cost of living in SF is high, but so is every major city in US. Quality of life better in SF Bay Area - worth every penny!